Stereogenic evolution of clasto-lactacystin β-lactone from L-serine

被引：25

作者：

Yoon, Cheol H. ^{[1
]}

Flanigan, David L.

Yoo, Kyung S.

Jung, Kyung W.

机构：

[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA

[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 01期

关键词：

stereoselctive C-H insertion; rhodium catalysis; gamma-lactam; aldol reaction; lactacystin beta-lactone;

D O I：

10.1002/ejoc.200600835

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein is a novel synthesis of clasto-lactacystin beta-lactone. The gamma-lactant core was selectively prepared by an intramolecular C-H insertion to establish the stereocenter, C(6). The ensuing construction of the quaternary C(5) and carbinol C(9) centers was facilitated by aldol with excellent stereos election. All these new stereo chemistries were induced by the inherent chirality Of L-serine without employing chiral auxiliaries or reagents. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

引用

页码：37 / 39

页数：3

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